Abstract
Hexachlorobutadiene (HCBD) was classed as a persistent organic pollutant under the Stockholm Convention in 2015. HCBD is mainly an unintentionally produced by-product of chlorinated hydrocarbon (e.g., trichloroethylene and tetrachloroethylene) synthesis. Few studies of HCBD formation during chemical production processes have been performed, so HCBD emissions from these potentially important sources are not understood. In this study, HCBD concentrations in raw materials, intermediate products, products, and bottom residues from chemical plants producing chlorobenzene, trichloroethylene, and tetrachloroethylene were determined. The results indicated that HCBD is unintentionally produced at much higher concentrations in trichloroethylene and tetrachloroethylene plants than chlorobenzene plants. The sum of the HCBD concentrations in the samples from all of the trichloroethylene and tetrachloroethylene production stages in plant PC was 247000 µg/mL, about three orders of magnitude higher than the concentrations in the tetrachloroethylene production samples (plant PB) and about six orders of magnitude higher than the concentrations in the chlorobenzene production samples (plant PA). The HCBD concentrations were highest in bottom residues from all of the plants. The concentrations in the bottom residue samples contributed 24%–99% of the total HCBD formed in the chemical production plants. The bottom residue, being hazardous waste, could be disposed of by incineration. The HCBD concentrations were much higher in intermediate products than raw materials, indicating that HCBD formed during production of the intended chemicals. The results indicate the concentrations of HCBD unintentionally produced in typical chemical plants and will be useful in developing protocols for controlling HCBD emissions to meet the Stockholm Convention requirements.
References
Barrek S, Crenolive C, Wiest L, Baudot R, Arnaudguilhem C, Grenierloustalot M (2009). Multi-residue analysis and ultra-trace quantification of 36 priority substances from the European Water Framework Directive by GC-MS and LC-FLD-MS/MS in surface waters. Talanta, 79(3): 712–722
Berger M, Schwarzbauer J (2016). Historical deposition of riverine contamination on terrestrial floodplains as revealed by organic indicators from an industrial point source. Water, Air, and Soil Pollution, 227(1): 20.1–20.14
Chang M B, Huang T F (2000). The effects of temperature and oxygen content on the PCDD/PCDFs formation in MSW fly ash. Chemosphere, 40(2): 159–164
Chen X, Luo Q, Wang D, Gao J, Wei Z, Wang Z, Zhou H, Mazumder A (2015). Simultaneous assessments of occurrence, ecological, human health, and organoleptic hazards for 77 VOCs in typical drinking water sources from 5 major river basins, China. Environmental Pollution, 206: 64–72
Cho E, Khim J, Chung S, Seo D, Son Y (2014). Occurrence of micropollutants in four major rivers in Korea. Science of the Total Environment, 491–492: 138–147
Denier van der Gon H, Van Het Bolscher M, Visschedijk A, Zandveld P (2007). Emissions of persistent organic pollutants and eight candidate POPs from UNECE-Europe in 2000, 2010 and 2020 and the emission reduction resulting from the implementation of the UNECE POP protocol. Atmospheric Environment, 41(40): 9245–9261
Duprat P, Gradiski D (1978). Percutaneous toxicity of hexachlorobutadiene. Acta Pharmacologica et Toxicologica, 43(5): 346–353
Fernandes A R, Mortimer D, Rose M, Smith F, Steel Z, Panton S (2019). Recently listed Stockholm convention POPs: Analytical methodology, occurrence in food and dietary exposure. Science of the Total Environment, 678: 793–800
Guo B, Meng J, Wang X, Yin C, Hao W, Ma B, Tao Z (2020). Quantification of pesticide residues on plastic mulching films in typical farmlands of the North China. Frontiers of Environmental Science & Engineering, 14(1): 2
Honing V D (2007). Exploration of management options for Hexachlorobutadiene (HCBD), in Paper for the 6th Meeting of the UNECE CLRTAP Task Force on Persistent Organic Pollutants. Vienna
Hu X, Yang T, Liu C, Jin J, Gao B, Wang X, Qi M, Wei B, Zhan Y, Chen T, Wang H, Liu Y, Bai D, Rao Z, Zhan N (2020). Distribution of aromatic amines, phenols, chlorobenzenes, and naphthalenes in the surface sediment of the Dianchi Lake, China. Frontiers of Environmental Science & Engineering, 14(4): 66
Huang H, Buekens A (2001). Chemical kinetic modeling of de novo synthesis of PCDD/F in municipal waste incinerators. Chemosphere, 44(6): 1505–1510
Juang D, Lee C, Chen W, Yuan C (2010). Do the VOCs that evaporate from a heavily polluted river threaten the health of riparian residents? Science of the Total Environment, 408(20): 4524–4531
Kong Q, Wang Y, Yang X (2020). A review on hexachloro-1,3-butadiene (HCBD): sources, occurrence, toxicity and transformation. Bulletin of Environmental Contamination and Toxicology, 104(1): 1–7
Lecloux A (2004). Hexachlorobutadiene-Sources, environmental fate and risk characterization. Science Dossier. Euro Chlor, Brussels, Belgium
Lee C, Song H, Fang M (2000). Concentrations of chlorobenzenes, hexachlorobutadiene and heavy metals in surficial sediments of Kaohsiung coast, Taiwan. Chemosphere, 41(6): 889–899
Li S, Zheng M, Liu W, Liu G, Xiao K, Li C (2014). Estimation and characterization of unintentionally produced persistent organic pollutant emission from converter steelmaking processes. Environmental Science and Pollution Research International, 21(12): 7361–7368
Li Y, Yang Y, Yu G, Huang J, Wang B, Deng S, Wang Y (2016). Emission of unintentionally produced persistent organic pollutants (UPOPs) from municipal waste incinerators in China. Chemosphere, 158: 17–23
Liu W, Zheng M, Wang D, Xing Y, Zhao X, Ma X, Qian Y (2004a). Formation of PCDD/Fs and PCBs in the process of production of 1,4-dichlorobenzene. Chemosphere, 57(10): 1317–1323
Liu W, Zheng M, Xing Y, Wang D (2004b). Polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans in 1,4-dichlorobenzene mothballs. Bulletin of Environmental Contamination and Toxicology, 73(1): 93–97
Liu X, Fiedler H, Gong W, Wang B, Yu G (2018). Potential sources of unintentionally produced PCB, HCB, and PeCBz in China: A preliminary overview. Frontiers of Environmental Science & Engineering, 12(6): 1
Logue J M, Mckone T E, Sherman M H, Singer B C (2011). Hazard assessment of chemical air contaminants measured in residences. Indoor Air, 21(2): 92–109
Matejczyk M, Plaza G A, Nalecz-Jawecki G, Ulfig K, Markowska-Szczupak A (2011). Estimation of the environmental risk posed by landfills using chemical, microbiological and ecotoxicological testing of leachates. Chemosphere, 82(7): 1017–1023
Pinto M I, Vale C, Sontag G, Noronha J P (2016). Pathways of priority pesticides in sediments of coastal lagoons: a case study of Obidos Lagoon, Portugal. Marine Pollution Bulletin, 106(1–2): 335–340
Sherry D, Mcculloch A, Liang Q, Reimann S, Newman P A (2018). Current sources of carbon tetrachloride (CCl4) in our atmosphere. Environmental Research Letters, 13(2): 024004
Solé M, Manzanera M, Bartolomé A, Tort L, Caixach J (2013). Persistent organic pollutants (POPs) in sediments from fishing grounds in the NW Mediterranean: Ecotoxicological implications for the benthic fish Solea sp. Marine Pollution Bulletin, 67(1–2): 158–165
Surma-Zadora M, Grochowalski A (2008). Using a membrane technique (SPM) for high fat food sample preparation in the determination of chlorinated persistent organic pollutants by a GC/ECD method. Food Chemistry, 111(1): 230–235
Tang Z, Huang Q, Cheng J, Qu D, Yang Y, Guo W (2014). Distribution and accumulation of hexachlorobutadiene in soils and terrestrial organisms from an agricultural area, East China. Ecotoxicology and Environmental Safety, 108: 329–334
Tang Z, Huang Q, Nie Z, Yang Y, Yang J, Qu D, Cheng J (2016). Levels and distribution of organochlorine pesticides and hexachlorobutadiene in soils and terrestrial organisms from a former pesticide-producing area in Southwest China. Stochastic Environmental Research and Risk Assessment, 30(4): 1249–1262
Tirey D A, Taylor P H, Kasner J, Dellinger B (1990). Gas phase formation of chlorinated aromatic compounds from the pyrolysis of tetrachloroethylene. Combustion Science and Technology, 74(1–6): 137–157
UNEP (2013). Report of the Persistent Organic Pollutants Review Committee on the Work of its Ninth Meeting: Risk Management Evaluation on Hexachlorobutadiene. Draft 2013. UNEP/POPS/POPRC.9/13/Add.2. United Nations Environment Programme, Rome, Italy
UNEP (2015). SC-7/12. Report of the Conference of the Parties to the Stockholm Convention on Persistent Organic Pollutants on the work of its seventh meeting. Draft 2015. UNEP/POPS/COP.7/36. United Nations Environment Programme Chemicals, Geneva, Switzerland
UNEP (2017). SC-8/12. Report of the Conference of the Parties to the Stockholm Convention on Persistent Organic Pollutants on the work of its eighth meeting. Draft 2017. UNEP/POPS/COP.8/32. United Nations Environment Programme Chemicals, Geneva, Switzerland
USEPA (2017). Preliminary Information on Manufacturing, Processing, Distribution, Use, and Disposal. Hexachlorobutadiene. US Environmental Protection Agency, Office of Chemical Safety and Pollution Prevention, Washington, DC, USA
Wang L, Bie P, Zhang J (2018). Estimates of unintentional production and emission of hexachlorobutadiene from 1992 to 2016 in China. Environmental Pollution, 238: 204–212
Wehrmeier A, Lenoir D, Sidhu S S, Taylor P H, Rubey W A, Kettrup A, Dellinger B (1998). Role of copper species in chlorination and condensation reactions of acetylene. Environmental Science & Technology, 32(18): 2741–2748
Zhang H, Jiang L, Zhou X, Zeng T, He Z, Huang X, Chen J, Song S (2018b). Determination of hexachlorobutadiene, pentachlorobenzene, and hexachlorobenzene in waste incineration fly ash using ultrasonic extraction followed by column cleanup and GC-MS analysis. Analytical and Bioanalytical Chemistry, 410(7): 1893–1902
Zhang H, Shen Y, Liu W, He Z, Fu J, Cai Z, Jiang G (2019). A review of sources, environmental occurrences and human exposure risks of hexachlorobutadiene and its association with some other chlorinated organics. Environmental Pollution, 253: 831–840
Zhang H, Wang Y, Sun C, Yu M, Gao Y, Wang T, Liu J, Jiang G (2014). Levels and distributions of hexachlorobutadiene and three chlorobenzenes in biosolids from wastewater treatment plants and in soils within and surrounding a chemical plant in China. Environmental Science & Technology, 48(3): 1525–1531
Zhang R, Yin R, Luo Y (2018b). Inhibition of C-Cl formation during the combustion of MSW gasification syngas: An experimental study on the synergism and competition between oxidation and chlorination. Waste Management (New York, N.Y.), 76: 472–482
Zhao X, Li J, Lu K, Huang X (2015). Characterization of particle/gas partition, congener patterns, and TEQ of PCBs and PCNs released from a municipal solid waste incinerator (MSWI) in South China. Environmental Chemistry, 34(7): 1268–1274
Acknowledgements
This work was supported by the National Natural Science Foundation of China (Grant Nos. 21936007 and 21906165), the CAS Interdisciplinary Innovation Team (Grant No. JCTD-2019-03), and the Youth Innovation Promotion Association of the Chinese Academy of Sciences (Grant No. 2016038).
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Highlights
• Unintentional HCBD production in typical chemical plants was investigated.
• The highest HCBD concentrations were found in the bottom residue.
• Tri/tetrachloroethylene production processes were important HCBD sources.
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Wang, M., Yang, L., Liu, X. et al. Hexachlorobutadiene emissions from typical chemical plants. Front. Environ. Sci. Eng. 15, 60 (2021). https://doi.org/10.1007/s11783-020-1352-8
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DOI: https://doi.org/10.1007/s11783-020-1352-8